HCID 178467676, compound → HCID 178419719, compound

HRID 1262650Notes

Reaction equation

HRID 1262650 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([C:10](OCC)([O:13]CC)[CH2:11][Br:12])[N:9]=1)[C:2]([NH2:4])=[NH:3]>Br>[BrH:12].[Br:12][CH2:11][C:10]([C:8]1[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=1)=[O:13]

Participants

3

Reactant 1

HCID 178467676HCID 178467676, compound

Product 1

HCID 178419719HCID 178419719, compoundYield 209.7%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 9.5 g (28 mmol) of 2-guanidino-4-(2-bromo-1,1-diethoxyethyl)thiazole in 50 ml of 48% hydrobromic acid was stirred at room temperature for 15 hours. The mixture was evaporated to complete dryness to afford 10.1 g (100%) of 2-bromo-1-(2-guanidino-4-thiazolyl)ethanone hydrobromide mp 247° (dec). This material could be converted to the free base by triturating with saturated sodium bicarbonate, stirring for 15 minutes, filtering the solid, and drying it under vacuum. In this way, 3.0 g of the hydrobromide salt was converted to 1.7 g (88%) of the free base, mp 210° (dec); nmr (DMSO-d6 (δ): 7.84 (s, 1H); 6.92 (s, 4H); 4.78 (s, 2H).

Workup

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-5faa47ee00784aca89e3798518b4fe49
Source dataset
uspto-grants-1984_06
Patent number
US04452987

Reaction notes

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